GB1287601A - Peptides and process for their manufacture - Google Patents

Peptides and process for their manufacture

Info

Publication number
GB1287601A
GB1287601A GB42272/69A GB4227269A GB1287601A GB 1287601 A GB1287601 A GB 1287601A GB 42272/69 A GB42272/69 A GB 42272/69A GB 4227269 A GB4227269 A GB 4227269A GB 1287601 A GB1287601 A GB 1287601A
Authority
GB
United Kingdom
Prior art keywords
tbu
thr
phe
asn
gly
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB42272/69A
Inventor
W Rittel
M Brugger
B Kamber
B Riniker
P Sieber
H M Greven
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH1306768A external-priority patent/CH559720A5/de
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1287601A publication Critical patent/GB1287601A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575Hormones
    • C07K14/585Calcitonins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biophysics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Endocrinology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

1287601 Calcitonin derivatives CIBA GEIGY AG 25 Aug 1969 [23 Aug 1968 27 Aug 1968 30 Aug 1968 10 Oct 1968 19 Nov 1968] 42272/69 Heading C2C Compounds (I) Met - Leu - Gly - Thr - Tyr - Thr - Gln - Asp- Phe - Asn - Lys - Phe - His - Thr - Phe - Pro- Gln . Thr - Ala - Ile - Gly - Val - Gly - Ala - Pro- NH 2 (I) (wherein R is H or a free or acylated amino group and the corresponding compounds in which independently of one another, one or more asparagine and glutamine residues are replaced by the aspartic or glutamic acid residues, respectively, end the aspartic acid residus is replaced by an asparagine residue), their dimers and acid addition salts and complexes of these compounds are prepared by (1) splitting off a protective group from a compound (I) or a dimer in which at least one amino or one carboxyl group is protected by such a group or (2) oxidizing the mercapto group which may be free or protected by trityl groups, to a disulphide bridge, in a compound (II) CH 2 SH R CH - CO - Gly - Asn - Leu - Ser - Thr- Cys - Met - Leu - Gly - Thr - Tyr - Thr - Gln- Asp . Phe - Asn - Lys - Phe - His - Thr - Phe- Pro - Gln - Thr - Ala - Ile - Gly - Val - Gly - Ala- ProNH 2 (II) or an analogue thereof or (3) condensing a compound of Formula (III) or (IV) (wherein the side chain amino group is optionally protected and in which A is 1 to 21 of the amino acid residue which follows Cys<SP>7</SP> and R is H or an acylated amino group, with the remaining sequence of the peptide, this sequence having an optionally protected side chain amino group and whose C-terminal amino acid is L- protine) and if desired converting a resulting free compound into an acid addition salt or complex thereof. The free acid dotricosopeptide derived from calcitonin M (the amide) is also disclosed together with its preparation. The following compounds are prepared as starting materials and intermediates: Z-Asn-Leu- OMe, H - Asn - Leu - OMe, Z - and H - Gly. Asn - Leu - OMe, BOC - Cys(TRI) - Gly - Asn- Leu - OMe and - NHNH 2 ; BOC - and HMet - Leu - GlyOMe, TRI - and H - Cys(TRI )- Met - Leu - GlyOMe, H - Cys(TRI) - Met - Leu- GlyOH, HThr(tBu)OMe, DPC - Ser(tBu) - Thr- (tBu) - OMe and NHNH 2 , DPC - Ser(tBu)Thr- (tBu) - Cys(TRI) - Met - Leu - Gly - OMe and - OH, H - Ser(tBu) - Thr(tBu) - Cys(TRI) - Met- Leu - Gly OH, BOC - Cys(TRI ) - Gly - Asn - Leu- Ser - (tBu) - Thr(tBu) - Cys(TRI) - Met - Leu- Thr(tBu) - Cys - Met - Leu - Gly - OH, Z - and H - Asp(OtBu) - PheOMe, Z - and H - Gln- Asp(OtBu) - Phe - OMe, Z - and H - Thr(tBu)- Gln - Asp(OtBu)PheOMe, Z - and H - Tyr(tBu)- Thr(tBu) - Gln - Asp(OtBu) - PheOMe and -NHNH 2 , Z - Lys(BOC) - Phe - OMe and NHNH 2 , Z - and H - Lys - (BOC) - Phe - His- OMe, Z - Asn - Lys(BOC) - Phe - His - OMe and - NHNH 2 , Z - Thr(tBu) - Phe - ProOH, Z- and H - Ile - Gly - OMe, Z - and H - Ala - Ile- Gly - OMe, Z - and H - Thr(tBu) - Ala - lie - Gly- OMe, H - Thr(tBu) - Ala - Ile - GlyOH, Z - and H - Gln . Thr(tBu) - Ala - lie - GlyOH, Z - and H - Thr(tBu) - Phe - Pro - Gin - Thr(tBu) - Ala- Ile - GlyOH, Z - and H - Asn - Lys(BOC) - Phe- His - Thr(tBu) - Phe - Pro - Gln - Thr(tBu) - Ala- Ile - GlyOH, Z - Thr(tBu) - Tyr(tBu) - Thr(tBu)- Gln - Asp(OtBu) - Phe - Asn - Lys(BOC) - Phe- His - Thr(tBu) - Phe - Pro - Gln - Thr(tBu) - Ala- Ile - GlyOH, Z - Ala - ProNH 2 , Z - and HGly - Ala - ProNH 2 , Z - and H - Val - Gly - Ala- ProNH 2 , and Z - and H - Thr(tBu) - Tyr(tBu)- Thr(tBu) - Gln - Asp(OtBu) - Phe - Asn- Lys(BOC) - Phe - His - Thr(tBu) - Phe - Pro- Gln - Thr(tBu) - Ala-Ile - Gly - Val - Gly- Ala - Pro - NH 2 , Z and H - Gln - Asn- Phe - OMe Z - and H - Thr - (tBu)- Gln - Asn - Phe - OMe, Z - and H - Tyr- (tBu) - Thr(tBu) - Gin - Asn - Phe - OMe, ZThr(tBu) - Tyr(tBu) - Thr(tBu) - Gln - Asn - Phe- OMe - and NHNH 2 , Z - Thr(tBu) - Tyr(tBu)- Thr(tBu) - Gln - Asn - Phe - Asn - Lys(BOC)- Phe - His - Thr(tBu) - Phe - Pro - Gln - Thr(tBu)- Ala - Ile - Gly - OH and Z and H - Thr(tBu)- Tyr(tBu) - Thr(tBu) - Gin - Asn - Phe - Asn - Phe- Asn - Lys(BOC) - Phe - His - Thr(tBu) - Phe- Pro - Gln - Thr(tBu) - Ala - Ile - Gly - Val - Gly- Ala - Pro - NH 2 . H - and DPC - Ser(tBu) - Thr- (tBu) - Cys(TRI) - OH, Z - Thr(tBu) - Tyr(tBu)- Thr(tBu) - Gln - Asp(OtBu) - Phe - OMe and - NHNH2, H - Phe - Pro - OH, Z - Thr(tBu) - Phe- Pro - OH, Z - Gln - Thr(tBu) Ala - Ile - Gly OMe, H - Gln - Thr(tBu) - Ala - Ile-Gly OMe, H - and Z - Gln - Aso - PheOMe, Z - and H - Thr(tBu)- Gln - Asn - PheOMe, Z - and H - Tyr(tBu)- Thr(tBu) - Gln - Asn - Phe - OMe, Z - Thr(tBu)- Tyr(tBu) - Thr(tBu) - Gln - Asn - Phe - OMe, - NHNH 2 , Z - Thr(tBu) - Tyr(tBu) - Thr(tBu). Gln - Asn - Phe - Asn - Lys(BOC) - Phe - His- Thr(tBu) - Phe - Pro - Gln - Thr(tBu) - Ala - Ile- Gly - OH, H - and Z - Thr(tBu) - Tyr(tBu)- Thr(tBu) - Gin - Asn - Phe - Asn - Lys(BOC)- Phe - His - Thr(tBu) - Phe - Pro - Gln - Thr(tBu)- Ala - Ile - Gly - Val - Gly - Ala - ProNH 2 . H - and TRI - Cys(TRI ) - Gly - Asn - LeuOMe. Ac- Cys(TRI ) - Gly - Asn - Leu - OMe and - NHNH 2 . Ac - Cys(TRI) - Gly - Asn - Leu - Ser(tBu) - Thr- Gly - Asn - Leu - Ser(tBu) - Thr(tBu)Cys - Met. Leu - GlyOH, Bmp(TRI)OH, Bmp(TRI )Gly. Asn - LeuOMe and - NHNH 2 . Bmp(TRI)- Gly - Asn - Leu - Ser(tBu) - Thr(tBu) - Cys(TRI )- Ser(tBu) - Thr(tBu)Cys - Met - Leu - GlyOH. HPro - OtBu, Z - and H - Ala - Pro - OtBu, Z - and H - Gly - Ala - Pro - OtBu, Z - and HVal - Gly - Ala - Pro - OtBu, H - Thr(tBu) - Tyr- (tBu) - Thr(tBu) - Gln - Asp(OtBu) - Phe - Asn- Lys(BOC) - Phe - His - Thr(tBu) - Phe - Pro- Gly - Asn - Leu - Ser(tBu) - Thr(tBu) - Gys - Met- Leu Gly - Thr(tBu) - Tyr(tBu) - Thr(tBu) - Gln- Asp(OtBu) - Phe - Asn - Lys(BOC) - Phe - His- Thr(tBu) - Phe - Pro - Gin - Thr(tBu) - Ala - Ile- GlyOH. BOC - Ser - Thr - OBzl, H - Ser - Thr- OBzl, BOC and H - Leu - Ser - Thr - OBzl, BOC - and H - Asn - Leu - Ser - ThrOBzl, BOCGly - Asn - Leu - Ser - Thr - OBzl, and OH, BOC - Gly - Asn - Leu - Ser - Thr - Cys(Bzl]- NHNHZ, H - Cys - Asn - Leu - Ser - Thr - Cys- (Bzl) - NHNHZ, BOC - Cys(Bzl) - Gly - Asn- Leu - Ser - Thr - Cys(Bzl) - NHNHZ. BOCCys - Gly - Asn - Leu - Ser - Thr - CysNHNH 2 . Cys - NHNH 2 , H - Leu - GlyOtt, BOC - Met- Leu - GlyOtt and OH, H - Met - Leu - Gly - OH, BOC - Cys - Gly - Asn - Leu - Ser - Thr - Cys- Met - Leu - GlyOH. Palmitic acid (Pal) - and lauric acid (Lau) para-nitrophenyl esters, Pal- and Lau - Cys(TRI) - Oly - Asn - Leu - OMe and -NHNH 2 , Pal- and Lau-Cys(TRI)-Gly-Asn- Leu - Ser(tBu) - Thr(tBu) - Cys(TRI ) - Met - Leu- Leu - Ser(tBu) - Thr(tBu) - Cys - Met - Leu - Gly- OH. BOC - Cys(TRI) - Gly - Asa - Leu - Ser. (tBu) - Thr(tBu) - Cys(TRI) - Met - Leu - Gly- Thr(tBu) - Tyr(tBu) - Thr(tBu) - Gln - Asp- (OtBu) - Phe - Asn - Lys(BOC) - Phe - His - Thr- (tBu) - Phe - Pro - Gln - Thr(tBu} - Ala - Ile - Gly- Asn - Leu - Ser(tBu) - Thr(tBu) - Cys - Met - Leu- Gly - Thr(tBu) - Tyr(tBu) - Thr(tBu) - Gln - Asp- (OtBu) - Phe - Asn - Lys(BOC) - Phe - His - Thr- (tBu) - Phe - Pro - Gln - Thr(tBu) - Ala - Ile - Gly- OH. Calcitonin. M and Asn<SP>15</SP>-calcitonin M where any free NH 2 is blocked by BOC, OH by tBu and COOH by COOtBu and N<SP>α</SP>-acetyl, palmitoyl and lauryl-calcitonin M similarly blocked. Pharmaceutical compositions in forms suitable for oral or parenteral administration and useful as hypocalcaemic agents contain peptides (I).
GB42272/69A 1968-08-23 1969-08-25 Peptides and process for their manufacture Expired GB1287601A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH1269168 1968-08-23
CH1281168 1968-08-27
CH1306768A CH559720A5 (en) 1968-08-30 1968-08-30
CH1514768 1968-10-10
CH1723568 1968-11-19

Publications (1)

Publication Number Publication Date
GB1287601A true GB1287601A (en) 1972-09-06

Family

ID=27509452

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42272/69A Expired GB1287601A (en) 1968-08-23 1969-08-25 Peptides and process for their manufacture

Country Status (9)

Country Link
JP (2) JPS4843751B1 (en)
BE (1) BE737890A (en)
DE (1) DE1941511C2 (en)
DK (1) DK129228B (en)
FR (1) FR2016253A1 (en)
GB (1) GB1287601A (en)
NL (1) NL163772C (en)
SE (2) SE374357B (en)
YU (2) YU35344B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161522A (en) 1975-04-04 1979-07-17 The Regents Of The University Of California Method for blocking allergic responses

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH594608A5 (en) * 1973-12-14 1978-01-13 Ciba Geigy Ag

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161522A (en) 1975-04-04 1979-07-17 The Regents Of The University Of California Method for blocking allergic responses

Also Published As

Publication number Publication date
JPS4839955B1 (en) 1973-11-28
FR2016253A1 (en) 1970-05-08
YU216769A (en) 1980-09-25
DE1941511C2 (en) 1982-11-18
SE365204B (en) 1974-03-18
JPS4843751B1 (en) 1973-12-20
NL163772B (en) 1980-05-16
YU36487B (en) 1984-02-29
SE374357B (en) 1975-03-03
YU201777A (en) 1982-02-25
YU35344B (en) 1980-12-31
NL163772C (en) 1980-10-15
DK129228B (en) 1974-09-16
BE737890A (en) 1970-02-23
DE1941511A1 (en) 1971-03-04
NL6912864A (en) 1970-02-25
DK129228C (en) 1975-02-17

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years